S$ 446 Find Cheap Flights from Chicago to Singapore

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to Singapore departing on 4-2. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to Singapore

Travellers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 25% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Free to useThere are no hidden charges or fees.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Chicago to Singapore

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for return flights from Chicago to Singapore that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent return flight deals from Chicago to Singapore

Tue, 20 Jan - Thu, 22 Jan
Multiple Airlines Logo
10:35 - 13:05
MDW
-
SIN
36h 30m2 stops
Multiple Airlines Logo
02:00 - 22:50
SIN
-
MDW
34h 50m2 stops
S$ 1,652Multiple Airlines
Tue, 27 Jan - Tue, 3 Feb
Multiple Airlines Logo
11:10 - 13:05
MDW
-
SIN
35h 55m3 stops
Multiple Airlines Logo
16:50 - 12:35
SIN
-
MDW
33h 45m2 stops
S$ 1,655Multiple Airlines
Mon, 30 Mar - Wed, 8 Apr
Multiple Airlines Logo
19:50 - 07:40
ORD
-
SIN
22h 50m1 stop
Multiple Airlines Logo
14:00 - 23:58
SIN
-
ORD
22h 58m2 stops
S$ 1,659Multiple Airlines
Thu, 12 Feb - Sun, 22 Feb
Delta Logo
06:00 - 05:00
MDW
-
SIN
33h 00m2 stops
Delta Logo
22:30 - 17:45
SIN
-
MDW
33h 15m2 stops
S$ 1,661Delta
Fri, 3 Apr - Mon, 13 Apr
Air Canada Logo
14:50 - 05:15
ORD
-
SIN
25h 25m2 stops
Air Canada Logo
09:50 - 14:43
SIN
-
ORD
41h 53m2 stops
S$ 1,672Air Canada
Thu, 19 Mar - Sat, 28 Mar
Delta Logo
06:30 - 05:00
MDW
-
SIN
33h 30m2 stops
Delta Logo
22:30 - 16:53
SIN
-
MDW
31h 23m2 stops
S$ 1,678Delta
Sat, 4 Apr - Wed, 15 Apr
Ethiopian Air Logo
10:15 - 07:30
ORD
-
SIN
32h 15m2 stops
Ethiopian Air Logo
15:10 - 08:15
SIN
-
ORD
54h 05m3 stops
S$ 1,678Ethiopian Air
Wed, 8 Apr - Sat, 11 Apr
Ethiopian Air Logo
10:15 - 07:30
ORD
-
SIN
32h 15m2 stops
Ethiopian Air Logo
15:10 - 08:15
SIN
-
ORD
54h 05m3 stops
S$ 1,709Ethiopian Air
Tue, 7 Apr - Thu, 9 Apr
EVA Air Logo
00:30 - 12:00
ORD
-
SIN
22h 30m1 stop
EVA Air Logo
15:10 - 05:54
SIN
-
ORD
27h 44m2 stops
S$ 1,726EVA Air
Tue, 6 Jan - Sun, 18 Jan
EVA Air Logo
13:09 - 12:05
ORD
-
SIN
32h 56m2 stops
EVA Air Logo
15:45 - 19:35
SIN
-
ORD
41h 50m1 stop
S$ 1,767EVA Air
Booking Insights

KAYAK's insights & trends for Chicago to Singapore flights

Get data-powered insights and trends into flights from Chicago to Singapore to help you find the cheapest flights, the best time to fly, and much more.

What is the cheapest month to fly from Chicago to Singapore?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago to Singapore, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Chicago to Singapore is February, when tickets cost S$ 1,033 (return) on average. On the other hand, the most expensive months are December and June, when the average cost of return tickets is S$ 2,468 and S$ 1,842 respectively.

What’s the cheapest day of the week to fly from Chicago to Singapore?

The average price of all round-trip flights from Chicago to Singapore clicked on KAYAK for each day over the last 12 months.

When flying from Chicago to Singapore, you should consider leaving on a Wednesday and avoid Saturdays if you are looking for the best rates. For your return to Chicago, you’ll find the best rates on Tuesdays and the most expensive ones on Sundays.

How far in advance should I book a flight from Chicago to Singapore?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Chicago to Singapore, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below-average price on the flight from Chicago to Singapore, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 16 weeks before departure.

Find deals

Good to know

Low seasonFebruary
Cheapest flightS$ 446
Best time to beat the crowds (30% less expensive on average)
Most popular time to fly (68% more expensive on average)
Flight from Chicago O'Hare Airport to Singapore

FAQs - booking Singapore flights

  • How does KAYAK find such low prices on flights from Chicago to Singapore?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago to Singapore.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago to Singapore?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Chicago to Singapore is likely to change within 7 days, so travellers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago to Singapore?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional return ticket. You could then fly from Chicago to Singapore with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago to Singapore?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying from Chicago to Singapore up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • What is the cheapest time of day to fly to Singapore?

    The cheapest time of day to fly to Singapore is generally in the evening, when retur flights cost S$ 2,321 on average. Morning departures are around 28% more expensive than evening flights, on average. The most expensive time of day to fly to Singapore is generally in the morning, which is peak travel time and where the average cost of a ticket is S$ 2,980.

Reviews of the top airline flying from Chicago to Singapore

 
Need help choosing which airline to fly with from Chicago to Singapore? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.4
United AirlinesOverall score based on 9095 reviews
7.3Comfort
8.1Crew
6.6Food
7.7Boarding
7.1Entertainment
Airline reviews

The movies offered were great. Staff were very pleasant and very efficient.

10.0 ExcellentAnonymous, Dec 2025
ORD - HND
Read more United Airlines reviews

The movies offered were great. Staff were very pleasant and very efficient.

After a delay at the gate, C3, at Ohare on Sunday, I left my Blk ski coat on the bench at the gate, lost! Please review my lob claim, thx.

Very nice flight love the small aircraft. We had a wonderful flight attendant. Nice to see someone that really enjoys her job. Don't have her name but had a southern accent.

Very thoughtful flight attendant offered me water immediately since I had run to make my connection.

Seats in waiting area and on plane hard as rock. Fast internet on the flight was great! Crew was kind.

Always wish for more healthy, gluten free options. We have to bring our own.

Having a long layover, I was very appreciative of the ability to stand by for an earlier flight. Other airlines like Delta have refused this to me in the past, just to be mean (because my ticket class wasn't high enough). United went out of their way to help me get to my destination early, which I really appreciated given that it was the third leg of a 24+ hour journey for me.

Other than a way way too cold cabinets for the entire flight, all was great

One bag is incorrect and not acceptable for an international flight. The food was not just good. I won't fly with them again.

Excellent flight. Smooth, efficient boarding. Quick flight. Arrived early at STL.

Everything you need to know for your flight from Chicago to Singapore

Cabin class types available on flights to Singapore

Cabin classes available on flights to Singapore. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.
First Class flights from Chicago to Singapore
Business Class flights from Chicago to Singapore
Prem Econ Class flights from Chicago to Singapore
Economy class flights from Chicago to Singapore